2,4,6-Trifluoroaniline → 2-(2,4,6-Trifluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

HRID 1288041Notes

Reaction equation

HRID 1288041 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[NH2:4].[CH:11]12[C:20](=O)[O:19][C:17](=[O:18])[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16]2>C(O)(=O)C>[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[C:5]([F:10])[C:3]=1[N:4]1[C:17](=[O:18])[CH:12]2[CH:11]([CH2:16][CH2:15][CH2:14][CH2:13]2)[C:20]1=[O:19]

Participants

4

Reactant 2

HCID 677652,4,6-TrifluoroanilineHCID 85689Hexahydrophthalic anhydride

Product 1

HCID 203847012-(2,4,6-Trifluorophenyl)hexahydro-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

9.54 Parts of 2,4,6-trifluoroaniline were added to a solution of 10 parts of cyclohexane-1,2-dicarboxylic anhydride in 100 parts of glacial acetic acid. The mixture was refluxed for 20 hours and the resulting mixture was poured into 200 parts of ice. The resulting crystals were filtered, dried and recrystallized twice from 70 parts of methanol at -40° C to yield 8.3 parts of white crystals of 2-(2,4,6-trifluorophenyl)-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione melting at 129°-131° C.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. additionthe resulting mixture was poured into 200 parts of ice
  3. filtrationThe resulting crystals were filtered
  4. customdried
  5. customrecrystallized twice from 70 parts of methanol at -40° C

Sources & evidence

ORD record
ord-ac7d8bcc216440ed99a565f73ad5dd93
Source dataset
uspto-grants-1976_10
Patent number
US03987057

Reaction notes

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